This invention relates to a novel antioxidant composition and the process for making the same. Many phenolic type antioxidants have been known heretofore. For example, an article by A. R. Patel et al, in Journal of Applied Polymer Science 16 (1972) at pages 2751-2763, describes the compound 6-(4-hydroxy-3,5-di-tertiarybutylanilino)-2,4-bis(n-octylthio)-1,3,5 triazine, which is mentioned as the mot effective antioxidant for the stabilization of polybutadiene rubber.
U.S. Pat. No. 3,334,046 also teaches the existance of 2,6-disubstituted phenolic antioxidants which are in the 4-position attached to a triazine compound. British Patent Specification No. 1,345,988 teaches a process for the preparation of compounds having the formula ##STR3##
wherein R.sub.1 and R.sub.2 are tertiary butyl, isopropyl, cyclohexyl, or phenyl and R.sub.3 is an organic radical. The preparation of such compounds generally comprises adding, dropwise, concentrated sulphuric acid to a heated solution of hydroquinone and the alcohol derived from R.sub.3. When the alcohol derived from R.sub.3 contains 10 or more carbon atoms such as a process is very difficult to practice commercially due to the formation of many by-products and the very slow reactionary. Thus, when R.sub.3 contains 10 or more carbon atoms, it is preferred to use a process in which the hydroquinone is reacted with an alkyl bromide in the presence of a weak base such as potassium bicarbonate and then a solvent such as cellosolve. Compounds in which R.sub.3 contains an alkyl group with 10 or more carbon atoms is especially suitable for protecting polyolefins from oxidation, not only during initial processing, but also thereafter. The compound 6-(4-hydroxy-3,5 -di-tertiarybutylanilino)-2,4-bis(n-octylthio)-1,3,5 triazine, which is described in the article by A. R. Patel et al, is marketed by CIBA-GEIGY under the trade name Irganox 565. For the stabilization of polypropylene, however, it is preferred to use tetrakis [3-(3,5-di-tertiarybutyl-4-hydroxyphenyl)propionyloxymethyl] methane, which is marketed by CIBA-GEIGY under the trade mark Irganox 1010. The foregoing is not surprising, considering the fact that the triazine disclosed in the article by Patel et al. is very sensitive to oxidation and the two thioether groups have little resistance to U.V. degradation. The oxidation product of said triazine compound is colored, making the triazine compound unsuitable for many applications. Moreover, the permanent protection of various polymers, such as polypropylene, is difficult to affect with such triazine compounds due to the instability of the thioether groups upon exposure to the U.V. light of the solar spectrum.